Synthesis and application of novel nucleoside phosphonates and phosphoramidites modified at the base moiety
Autor(en): | Seela, F Chen, YM Melenewski, A Rosemeyer, H Wei, CF |
Stichwörter: | 2'-deoxyisoguanosine; 2-deoxyisoinosine; 5-aza-7-deaza-2'-deoxyguanosine; Biochemistry & Molecular Biology; CONFORMATION; FORMYCIN; N-1-methyl-2'-deoxyformycin A, B; oligodeoxyribonucleotides; OLIGONUCLEOTIDES; ORIGIN; PROTECTING GROUPS | Erscheinungsdatum: | 1996 | Herausgeber: | ACTA BIOCHIMICA POLONICA | Journal: | ACTA BIOCHIMICA POLONICA | Volumen: | 43 | Ausgabe: | 1 | Startseite: | 45 | Seitenende: | 52 | Zusammenfassung: | The H-phosphonates and phosphoramidites of 2'-deoxyisoguanosine, 2'-deoxyisoinosine, 5-aza-7-deaza-2'-deoxyguanosine, and N-1-methyl-2'-deoxyformycin A were prepared. The diphenylcarbamoyl group was chosen for the 2-O-protection of 2'-deoxyisoinosine and 2'-deoxyisoguanosine, and dimethylaminoalkylidene groups were used to block the amino function of the various monomers. The synthesis of isoguanine oligonucleotides was found to be much more efficient using the 2-O-protected building blocks compared to those without oxygen protection. Oligodeoxynucleotides containing 2'-deoxyisoguanosine and 2'-deoxycytidine form parallel duplex structures. The self-complementary duplex containing 5-aza-7-deaza-2'-deoxyguanosine and 2'-deoxycytidine forms a stable duplex in acidic solution (pH = 5.0) while it is destabilized under neutral conditions. |
Beschreibung: | Symposium on Structure and Biological Functions of Nucleic Acid Components and Their Analogues, and Related Topics, WARSAW, POLAND, SEP 02-05, 1995 |
ISSN: | 0001527X |
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